Which hat’s a winner for the races?

ISABEL OAKESHOTT used to hate headwear. Then she got an Ascot invitation. So...

ACHANCE invitation to Royal Ascot thanks to a political contact throws up a dilemma: do I pass up the opportunity to hang out in the Royal enclosure on Ladies Day — where strict hat rules apply — or resign myself to sporting hair-crushing, scalp-itching and dignity-robbing headwear?

I’ve never been a hat person. I blame the teenage trauma of wearing a riding helmet. As a 14-year- old in grubby jodhpurs, I couldn’t carry off the hard hat look and I’ve been a hat dodger ever since. I dislike how they feel perched precariously on the head — and worry that, because I have a round face, I just can’t carry them off.

But the offer of a day at the races seems too good to refuse, so I draft in top British milliner Stephen Jones OBE — who has made hats for Sarah Jessica Parker, Jerry Hall and Princess Diana — in the hope that he can save my pride.

He tells me: ‘Many of us can go our entire lives without wearing anything more elaborate than a beach hat, so it’s daunting when an occasion suddenly demands something more formal — and no wonder.

‘A hat is so visible, you can’t escape from a bad one. That’s why it’s so important to take your time and try out lots of styles to see which best balances out both your facial features and your body shape.

‘Go into a store or borrow a friend’s and see how it looks — and how it feels. If you don’t feel comfortable in a hat, then it will show, even if the style suits your face. Wear it at home before its first outing — 90 per cent of carrying off a hat is feeling relaxed.’

So, with all this in mind, how did I fare — and could I be convinced to wear one?